DE1154894B - Verfahren zur Herstellung von in Wasser schwer- bis unloeslichen Methinfarbstoffen - Google Patents
Verfahren zur Herstellung von in Wasser schwer- bis unloeslichen MethinfarbstoffenInfo
- Publication number
- DE1154894B DE1154894B DEF27153A DEF0027153A DE1154894B DE 1154894 B DE1154894 B DE 1154894B DE F27153 A DEF27153 A DE F27153A DE F0027153 A DEF0027153 A DE F0027153A DE 1154894 B DE1154894 B DE 1154894B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- weight
- trimethyl
- methylene
- pyrazolone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000975 dye Substances 0.000 title claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 title claims description 5
- -1 aralkyl radicals disubstituted 2-methylene indolines Chemical class 0.000 claims description 8
- 150000002081 enamines Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000013078 crystal Substances 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- ZTUKGBOUHWYFGC-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylideneindole Chemical compound C1=CC=C2N(C)C(=C)C(C)(C)C2=C1 ZTUKGBOUHWYFGC-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 5
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- CVHDZBBLDJRKOS-UHFFFAOYSA-N methyl 1,3,3-trimethyl-2-methylideneindole-5-carboxylate Chemical compound COC(=O)C1=CC=C2N(C)C(=C)C(C)(C)C2=C1 CVHDZBBLDJRKOS-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- MKMDCEXRIPLNGJ-UHFFFAOYSA-N 2-phenyl-1h-pyrazol-5-one Chemical compound N1=C(O)C=CN1C1=CC=CC=C1 MKMDCEXRIPLNGJ-UHFFFAOYSA-N 0.000 description 2
- DSERYMNADDJALG-UHFFFAOYSA-N 4-(anilinomethylidene)-5-methyl-2-phenylpyrazol-3-one Chemical compound CC1=NN(C=2C=CC=CC=2)C(=O)C1=CNC1=CC=CC=C1 DSERYMNADDJALG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000005521 carbonamide group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- YYLKYJXVNOCHAW-UHFFFAOYSA-N 1,3,3,5-tetramethyl-2-methylideneindole Chemical compound CC1=CC=C2N(C)C(=C)C(C)(C)C2=C1 YYLKYJXVNOCHAW-UHFFFAOYSA-N 0.000 description 1
- MSYLUVZVKYDOBN-UHFFFAOYSA-N 1,3,3-triethyl-2-methylideneindole Chemical compound C1=CC=C2N(CC)C(=C)C(CC)(CC)C2=C1 MSYLUVZVKYDOBN-UHFFFAOYSA-N 0.000 description 1
- LDBCIMDXLNDQPJ-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylidene-5-methylsulfonylindole Chemical compound CS(=O)(=O)C1=CC=C2N(C)C(=C)C(C)(C)C2=C1 LDBCIMDXLNDQPJ-UHFFFAOYSA-N 0.000 description 1
- WHFGEAVJRDAMNU-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylidene-5-nitroindole Chemical compound [O-][N+](=O)C1=CC=C2N(C)C(=C)C(C)(C)C2=C1 WHFGEAVJRDAMNU-UHFFFAOYSA-N 0.000 description 1
- WHPVQSTYFPPYCQ-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylideneindol-5-amine Chemical compound NC1=CC=C2N(C)C(=C)C(C)(C)C2=C1 WHPVQSTYFPPYCQ-UHFFFAOYSA-N 0.000 description 1
- WCCZCMXUUXNPNI-UHFFFAOYSA-N 1,3,3-trimethyl-2-methylideneindole-5-carbonitrile Chemical compound N#CC1=CC=C2N(C)C(=C)C(C)(C)C2=C1 WCCZCMXUUXNPNI-UHFFFAOYSA-N 0.000 description 1
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- MWYTVFRHPLPLKF-UHFFFAOYSA-N 1-ethyl-3,3-dimethyl-2-methylideneindole Chemical compound C1=CC=C2N(CC)C(=C)C(C)(C)C2=C1 MWYTVFRHPLPLKF-UHFFFAOYSA-N 0.000 description 1
- JQBAXZPWFVBYRG-UHFFFAOYSA-N 1-phenyl-2-(1,3,3,5-tetramethylindol-2-ylidene)ethanone Chemical compound CC1(C)C2=CC(C)=CC=C2N(C)C1=CC(=O)C1=CC=CC=C1 JQBAXZPWFVBYRG-UHFFFAOYSA-N 0.000 description 1
- CBKKGONBCZOMHO-UHFFFAOYSA-N 2,3-dihydro-1H-pyrazole-4-carbaldehyde Chemical class N1NCC(=C1)C=O CBKKGONBCZOMHO-UHFFFAOYSA-N 0.000 description 1
- SDEKSCBERJHVOW-UHFFFAOYSA-N 2-(1,3,3,5-tetramethylindol-2-ylidene)acetonitrile Chemical compound CC1=CC=C2N(C)C(=CC#N)C(C)(C)C2=C1 SDEKSCBERJHVOW-UHFFFAOYSA-N 0.000 description 1
- PFVLVYNAIXBMRV-UHFFFAOYSA-N 2-(5-methoxy-1,3,3-trimethylindol-2-ylidene)acetonitrile Chemical compound COC1=CC=C2N(C)C(=CC#N)C(C)(C)C2=C1 PFVLVYNAIXBMRV-UHFFFAOYSA-N 0.000 description 1
- FDVITFMRUUGIBF-UHFFFAOYSA-N 2-methylidene-1,3-dihydroindole Chemical compound C1=CC=C2NC(=C)CC2=C1 FDVITFMRUUGIBF-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- VDMXGJJMPKAYQP-UHFFFAOYSA-N 5-chloro-1,3,3-trimethyl-2-methylideneindole Chemical compound ClC1=CC=C2N(C)C(=C)C(C)(C)C2=C1 VDMXGJJMPKAYQP-UHFFFAOYSA-N 0.000 description 1
- LHMPTDSCKKGDTG-UHFFFAOYSA-N 5-ethoxy-1-ethyl-3,3-dimethyl-2-methylideneindole Chemical compound C(C)OC=1C=C2C(C(N(C2=CC1)CC)=C)(C)C LHMPTDSCKKGDTG-UHFFFAOYSA-N 0.000 description 1
- BGXWEEHVMWADRH-UHFFFAOYSA-N 5-methoxy-1,3,3-trimethyl-2-methylideneindole Chemical compound COC1=CC=C2N(C)C(=C)C(C)(C)C2=C1 BGXWEEHVMWADRH-UHFFFAOYSA-N 0.000 description 1
- KWPOOQSDQSSHMW-UHFFFAOYSA-N CN1C(C(C2=CC(=CC(=C12)C)[N+](=O)[O-])(C)C)=C Chemical compound CN1C(C(C2=CC(=CC(=C12)C)[N+](=O)[O-])(C)C)=C KWPOOQSDQSSHMW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002084 enol ethers Chemical class 0.000 description 1
- JVSBIWJNYOTMRA-UHFFFAOYSA-N ethyl 4-(dimethylaminomethylidene)-5-oxo-1-phenylpyrazole-3-carboxylate Chemical compound O=C1C(=CN(C)C)C(C(=O)OCC)=NN1C1=CC=CC=C1 JVSBIWJNYOTMRA-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002476 indolines Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/10—The polymethine chain containing an even number of >CH- groups
- C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/06—Dyes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/924—Polyamide fiber
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL135944D NL135944C (en, 2012) | 1958-08-22 | ||
| NL242568D NL242568A (en, 2012) | 1958-08-22 | ||
| BE581913D BE581913A (en, 2012) | 1958-08-22 | ||
| DEF27153A DE1154894B (de) | 1958-08-22 | 1958-11-29 | Verfahren zur Herstellung von in Wasser schwer- bis unloeslichen Methinfarbstoffen |
| CH1266760A CH461681A (de) | 1958-08-22 | 1959-08-10 | Verfahren zur Herstellung von Methinfarbstoffen |
| GB1852762A GB929394A (en) | 1958-08-22 | 1959-08-21 | Process for dyeing or printing synthetic polymers |
| GB28738/59A GB929393A (en) | 1958-08-22 | 1959-08-21 | Methine dyestuffs |
| FR803267A FR1242941A (fr) | 1958-08-22 | 1959-08-21 | Colorants méthiniques et procédé de teinture |
| CH7678059A CH370046A (de) | 1958-08-22 | 1959-10-01 | Verfahren zum Färben und Bedrucken von synthetischen Fasern mit Methinfarbstoffen |
| US187149A US3184453A (en) | 1958-08-22 | 1962-04-10 | 3-dimethyl-substituted indoline dyestuffs |
| US187148A US3255204A (en) | 1958-08-22 | 1962-04-10 | Methine dyestuffs |
| US427205A US3441563A (en) | 1958-08-22 | 1965-01-05 | Process for the production of substituted pyrazolones and of monomethine dyestuffs thereof |
| NL7009979A NL7009979A (en) | 1958-08-22 | 1970-07-06 | Methine pigments |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0026470 | 1958-08-22 | ||
| DEF27153A DE1154894B (de) | 1958-08-22 | 1958-11-29 | Verfahren zur Herstellung von in Wasser schwer- bis unloeslichen Methinfarbstoffen |
| DEF0027223 | 1958-12-12 | ||
| US83518159A | 1959-08-21 | 1959-08-21 | |
| US187148A US3255204A (en) | 1958-08-22 | 1962-04-10 | Methine dyestuffs |
| US187149A US3184453A (en) | 1958-08-22 | 1962-04-10 | 3-dimethyl-substituted indoline dyestuffs |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1154894B true DE1154894B (de) | 1963-09-26 |
Family
ID=47605813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF27153A Pending DE1154894B (de) | 1958-08-22 | 1958-11-29 | Verfahren zur Herstellung von in Wasser schwer- bis unloeslichen Methinfarbstoffen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3184453A (en, 2012) |
| BE (1) | BE581913A (en, 2012) |
| CH (1) | CH370046A (en, 2012) |
| DE (1) | DE1154894B (en, 2012) |
| FR (1) | FR1242941A (en, 2012) |
| GB (1) | GB929393A (en, 2012) |
| NL (2) | NL135944C (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0087044A1 (de) * | 1982-02-19 | 1983-08-31 | Bayer Ag | Verfahren zum Färben thermoplastischer Kunststoffe in der Masse |
| EP0419110A1 (en) * | 1989-09-22 | 1991-03-27 | Sumitomo Chemical Company, Limited | Methine compound |
| US6465659B2 (en) | 2001-03-09 | 2002-10-15 | Bayer Aktiengesellschaft | Process for preparing asymmetrical methine dyes |
| WO2018043451A1 (ja) * | 2016-09-05 | 2018-03-08 | 株式会社Adeka | ポリメチン化合物 |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3844715A (en) * | 1972-12-29 | 1974-10-29 | American Aniline Prod | Polymeric materials colored with yellow methine dyes and pigments |
| CN106833007B (zh) * | 2017-01-16 | 2018-12-11 | 安徽清科瑞洁新材料有限公司 | 一种溶剂橙107染料的环保制备方法 |
| CN109053694B (zh) * | 2018-09-18 | 2020-06-26 | 宁波龙欣精细化工有限公司 | 一锅法制备吲哚啉系甲川染料的方法 |
| US11155884B1 (en) | 2020-10-16 | 2021-10-26 | Klemm & Sohn Gmbh & Co. Kg | Double-flowering dwarf Calibrachoa |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2032502A (en) * | 1930-09-10 | 1936-03-03 | Ici Ltd | Polymethine dyes containing a pyrazolone nucleus and process of producing them |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2280253A (en) * | 1935-04-26 | 1942-04-21 | Gen Aniline & Film Corp | Dyestuffs of the methine series |
| GB519895A (en) * | 1938-10-06 | 1940-04-09 | John David Kendall | Improvements in or relating to the sensitizing of photographic emulsions |
| NL53648C (en, 2012) * | 1939-11-27 | |||
| GB551718A (en) * | 1941-09-01 | 1943-03-08 | John David Kendall | Improvements in or relating to the production and use of dyestuffs |
| US2639282A (en) * | 1949-09-29 | 1953-05-19 | Eastman Kodak Co | Resin-dyes of the cyanine type |
| BE551825A (en, 2012) * | 1955-10-25 | |||
| BE576230A (en, 2012) * | 1958-03-04 |
-
0
- BE BE581913D patent/BE581913A/xx unknown
- NL NL242568D patent/NL242568A/xx unknown
- NL NL135944D patent/NL135944C/xx active
-
1958
- 1958-11-29 DE DEF27153A patent/DE1154894B/de active Pending
-
1959
- 1959-08-21 FR FR803267A patent/FR1242941A/fr not_active Expired
- 1959-08-21 GB GB28738/59A patent/GB929393A/en not_active Expired
- 1959-10-01 CH CH7678059A patent/CH370046A/de unknown
-
1962
- 1962-04-10 US US187149A patent/US3184453A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2032502A (en) * | 1930-09-10 | 1936-03-03 | Ici Ltd | Polymethine dyes containing a pyrazolone nucleus and process of producing them |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0087044A1 (de) * | 1982-02-19 | 1983-08-31 | Bayer Ag | Verfahren zum Färben thermoplastischer Kunststoffe in der Masse |
| DE3206091A1 (de) * | 1982-02-19 | 1983-09-01 | Bayer Ag, 5090 Leverkusen | Verfahren zum faerben thermoplastischer kunststoffe in der masse |
| EP0419110A1 (en) * | 1989-09-22 | 1991-03-27 | Sumitomo Chemical Company, Limited | Methine compound |
| US5136045A (en) * | 1989-09-22 | 1992-08-04 | Sumitomo Chemical Company, Limited | Pyrazole containing methine compounds |
| US6465659B2 (en) | 2001-03-09 | 2002-10-15 | Bayer Aktiengesellschaft | Process for preparing asymmetrical methine dyes |
| EP1239009A3 (de) * | 2001-03-09 | 2004-03-17 | Bayer Chemicals AG | Verfahren zur Herstellung von unsymmetrischen Methinfarbstoffen |
| WO2018043451A1 (ja) * | 2016-09-05 | 2018-03-08 | 株式会社Adeka | ポリメチン化合物 |
| CN109511264A (zh) * | 2016-09-05 | 2019-03-22 | 株式会社艾迪科 | 多次甲基化合物 |
| JPWO2018043451A1 (ja) * | 2016-09-05 | 2019-06-24 | 株式会社Adeka | ポリメチン化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| NL242568A (en, 2012) | 1958-11-20 |
| GB929393A (en) | 1963-06-19 |
| BE581913A (en, 2012) | |
| FR1242941A (fr) | 1960-10-07 |
| US3184453A (en) | 1965-05-18 |
| NL135944C (en, 2012) | |
| CH370046A (de) | 1963-03-15 |
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